One of my friends dad bought a 3-year old hurricane deck boat for 40,000 with cash around 2006-2007. Brand new, I think it was around $60,000. He sold it two years later for $12,000 in 2009.
I have an out of state friend that bought a boat in 2010 and is an elementary school teacher. Similar to the story above, he got a 3 year-old ski boat for $25,000. Brand new, it was probably $75,000.
He is on water 3-5 days/week during his 2.5 month summer vacation. He avoids the weekends because it is too crowded. Even when school starts in late August he still manages to get on the water 2-3 days/week after school. School is out at 2:30 and he is on the water around 3:30-4:00.
I have never seen someone get so much use out of a boat.